Water → HCID 11027585, compound

HRID 1648455Notes

Reaction equation

HRID 1648455 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)(=[O:10])[CH3:9].[C:26]1([C:32](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C(Cl)Cl.C(OCC)(=O)C>[C:8]([O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[N:19]([C:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:18]2=[O:23])=[CH:14][CH:13]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2818127HCID 2818127, compound

Product 1

HCID 11027585HCID 11027585, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3.43 g of triethylamine were added to a solution of 9.0 g of 5-(4-acetoxybenzyl)thiazolidine-2,4-dione [prepared as described in step (b) above] in 70 ml of methylene chloride, and a solution of 9.45 g of triphenylmethyl chloride in 30 ml of methylene chloride was added dropwise to the resulting mixture. The mixture was then stirred at room temperature for one hour, after which it was allowed to stand overnight at the same temperature. At the end of this time, the reaction mixture was mixed with water and ethyl acetate, and the organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crystals which separated were washed with a mixture of hexane and ethyl acetate and dried, to give 7.86 g of the title compound, melting at between 152° C. and 156° C. 11(d) 5-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

Workup

  1. waitto stand overnight at the same temperature
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe crystals which separated
  7. washwere washed with a mixture of hexane and ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-0b02de180da644a6a5db5d9e0b8cd6f0
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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